The Bet
by BigCityDreams4ever
Summary: What if Blair was new to the UES? That means she never met Nate or Serena ,and never met the biggest womenizer in the UES, Chuck Bass. One day Nate makes a bet with Chuck, if he can last one month going out with Blair and just her. C/B REPOSTED
1. Chapter 1

A/N: Hey! Whats up! Okay, this story is finally a Chair fanfic! Yay!! So of course Blair is new to the Upper East Side, but I'm not sure if I'm going to make her as Queen B. REMINDER:NO ONE KNOWS BLAIR YET!!!ANd i might have so mistakes like texting words.

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**Spotted: Looks like theres a new girl in the upper east side. A pettie brunette *gasp* with the new Mac Jacobs bag! Damn, this girl knows fashion. Watch out upper east siders. This girl looks like the new crazy bitch in town. She already looks like Queen. Looks can kill, but can she? Keep me posted.**

**You know you love me**

**xoxo,gossip girl**

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**B POV**

As i got out of the airport, everyone been stairing at like I'm like a crazy bitch. I wondered why. Later that day I checked out the penthouse and unpacked my things, and getting ready for my new school

I'll be going tommrow, my new school, Constance. Hopefully people there won't think I'm too perfect. I thought as i was picking out a headband to match with the schools' uniforms.

******(NEXT DAY)**

******(STIIL B POV)**

When I got to school people were stairing at me again, but I liked it. As I was walking, I was aporached by a tall beauitful blonde girl.

"Hi! I'm Serena Van der Woodsen." She greeted me nicely, " You must be Blair Waldorf."

"How do you know my name?" I asked her all confused.

" Gossip girl has been posting stuff about you like crazy"

"Oh."

"Gossip girl is the thing where you get your gossip,"Serena explaning it to me,"and she has been posting stuff about you lately."

"Oh, thanks for telling me this." I thanked her

"Sure thing, well i have to get to class, I'll meet you by the steps at lunch?'' Serena inviting me

"Oh, sure. That will be great." I said, taking her invite.

"Cool." Serena answered back as she walked away. I turned around and walked to find my class until someone bumped into me witch cost my bag and stuff flying everwhere and me falling. As I close my eyes

before I hit the ground. Someone caught me,and having that someone catching me with their hands on my ass.

"Ugh, watch where your going, bitch!"I shouted "and get you hands off my ass, you perv!"

"Oh, sorry." the mysteriest boy said.

When I looked up, I saw the most beauitful blue eyes I ever seen **(****hehe I bet you guys thought it was Chuck)**. Then I bent down to pick up my stuff. Then "he" helped me.

Thanks." I said as the guy gave me the last thing on the floor.

"Your welcome" the guy said with his nice and cute smile **(ok who cant help but smile when chace crawford smiles?)**

"I'm Nate be the way," he said,"and I'm not a perv, just letting you know."

"Oh, sorry for my bitchyness,"I apologizes to him."I'm Blair, Blair Waldorf."

"Well, nice to meet you Blair."taking my hand, helping me to get up for the floor,"So I'll see you around?

"I'll see what I can do." I told him,playing hard to get.

"Wow, your one of a kind, Blair Waldorf."Nate said all surprised, and watched me as I walked away.

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**A/N: Ok. So what do you think? Is it good,weird,or bad? Well Chuck is going to be in the next chapter, so its going to get intersing. Well I hoped you guy like it. Reviews are loved!!!!!! I'll try to update offen!!!!! Maybe the next chapter will be up around the weekends. And NO Nate is falling for Blair because this is a CHAIR story!!!!!And if anyone want to be my co writer just leave me message. Well thats all for now!!!!! Peace out and review!!!!!!!!**

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	2. Chapter 2

**A/N: Hey! Before I want to start the chapter I want to give a big thanks to xoxogg4lifexoxo,jjackieperez1,and thegoodgossipgirl who reviewed. You guy are awesome!!!!! Well in the last chapter I forgot to put gossip girl at the end,so I'm going to start the chapter off with it. Well, I hope you guys will enjoy this chapter!!!!**

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**Spotted:N getting his hands on the new girl, B. We ever knew that you can play, N. Any chances of you guys getting together? Well, keep me posted.**

**You know you love me,**

**xoxo,gossip girl**

**(C POV)**

**(At lunch)**

I was in the courtyard making out with a random girl, I didn't even know, but hey I'm Chuck Bass. I'm the biggest womenizer in the Upper East Side. Girls are like klenexes, use once and then throw away.

"Hey man."Nate greeted me.

"Whats up." I greeted back.

Then Nate glared at the girl, then back at me giving me the get-rid-of-the girl look.

"Oh Jessica, your dismiss." guessing her name.

"My name is Bella!"(What? I couldn't think of a name.)

"Yea, whatever." Ignoring her.

As she walked away Nate asked,

" Dude, how many girls have have you been with,this whole week?"

"Oh, about 12 I think."

"12?"Nate asked.

"So?"telling him,"I'm Chuck Bass."

"Of,couse." Nate said, always use to that answer.

As Nate went on and on about how I move girl to girl like every hour,and how it won't get me anywhere. As I looked around the courtyard, cause I got bored of Nate's speech about not using girl, then someone caught me eye. She was hot! I mean I been with a lot of girls but this one was different.

"Who is she?" I asked Nate, staring at the brunette.

"Oh, thats Blair Waldorf." Nate told me with a smile.

"Oh, I have to tap that ass." I answered back while i was checking her out.

"I happenly did." Nate said with a big smile like a little kid.

"What?'' I asked with a shocked face.

"Well something like that, chuck your phone."

As I got out my phone and opened it, I got a new message from gossip girl, of couse. Then I saw a picture of Nate and her. In the picture Nate was all over her, I mean her chest was on his and his hands were on her ass!

"Well Nathaniel, I never knew you can play." I said with a smirk, "now excuse me, I'm going to hit my new target." Looking at the beauitful brunette.

"Wait Chuck, I don't think you want to go there man."

"Cause she's different, she lays hard to get." Nate explained.

"Well, I'm Chuck Bass, and I'm always up for a challgen," As I walked over to the girl.

"Well, don't come running to me a say I didn't warn you." Nate called.

"Yea yea yea." Ignoring Nate

As I walked up to her I said,

"Well, hello beauiful."

After I said that I expected a laugh or her to blush and turning away, so I wouldn't see. But instead she said,

"Ew, Your such a pig."

Then I was frozen. I was shocked that she didn't fall for that move. But I wasn't going to let her get away. I had to beat this girl at her own game.

"Well, I'm Chuck Bass."

"Yea, whatever."she said, not paying attention to me at all.

"You know what Waldorf, your a bitch." Yea I said it, the one word that gets every girl mad.

"You think that will bug me, Bass?"She asked as she got up to my level,"Bitch is my nickname."

Whit those words I can tell that she was finished with the game, so I walked away, back to Nate. As I walked walked to the spot, Nate was laughing his face off.

"Shut up," I told him.

"Oh, sorry man, but she barried you good."

"I told you she's different."

"Well she won't be different when she wants to sleep with me." I said with a smirk.

"So your trying to have sex with her?" Nate asked all confused.

"Um.. Hello Nathaniel, have you seen her?"

"Yeah, but how can you try to have sex with her, without her beating you at your game?"

" Well, she just has to try not to piss me off."

"Ha, I bet you can't last even last a day with her." Nate laughed.

"Oh, yea?" I asked, chanllgening him.

"Yea, and change the one day to month."Nate said, "and also you have to date her,and only her, which means no sleeping with other girls."

"Whoa whoa whoa, Chuck Bass dose not do dates." I said

"But this will help you on relationships." Nate responed

"I don't do relationship also." I said with a discussed look on my face.

"What? Your scared to lose?" Nate said

"Oh, its on." I told him, giving him a glare.

**Spotted: N and C making a bet. It looks like it has to do with our very own new girl, B. After B beating C at his game? Looks like this bet is going to get intersing. Play safe kitties. Until then, keep me posted.**

**You know you love me,**

**xoxo gossip girl**

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**A/N: Thanks again for the reviews!!!! They make my day. Well help me think of two punishments for Nate and Chuck when one of then loses the bet! Remember to review cause reviews will help me update offen!!! Well I hope you guys a great summer. Reviews will be loved! Peace out!!**

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	3. Chapter 3

**Hey you guys!! Sorry about the long wait. I kinda got stuck on some parts. Thank you so much for all the reviews!!!!! You guys make my day. SO yea. Here it is!!! Chapter 3 to The Bet. Just letting you know this too so long to write. I mean I started the chapter on July 4 and just finished it just yesterday. So it pretty much took 22 days to write this.**

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**C'S POV**

What have I done? I just made a bet with Nate to date a girl for a month!! I mean who is crazy to do that? Now I have to date this bitchy and a hot brunette

with the most prettiest eyes. Oh, God, I'm so whip. This is so not worth Nate selling his Volvo (yes Twilighters, the one Edward has) if I win. And if I lose

Nate gets my limo. I mean what do I do if I don't have my limo? Walk? Or use a cab? Chuck Bass dose not walk or ride in cabs as transportation. I have to get

this girl to want me. Ugh. Then I guess I have to get to know her.

As the bell rang, I walked to my English class, Once I walked in the classroom, I saw the brunette.

"Well I see we meet again." I said with a smirk.

"Shut up Bass." she snapped

"Touche` with the last name thing, Waldorf."

"Yeah, yeah, yeah." Blair said ignoring me.

Before class started, everyone was already in class. I noticed everyone was staring at Blair. All the guys were checking her out, winking at her, while all of the

girls were getting jealous. A few minutes later, I noticed Jesse, I think it was, walking over to Blair.

"Hey, I'm Jesse" I over heard.

"I'm Blair." she said with with a fake smile.

"I was just wondering is you would like to get a drink with me with me tonight?"

"Sure, I would love to." she answered back.

"Cool, so I'll call you?" He said while giving her a pen for her to write down her number on is arm.

""Yeah." She replied

As Jesse walked back to his seat, he gave her a wink, then I gave him a death glare. Then I thought in my head This is going to be a long day to even get the chance to talk to her, since every guy is like grouping her. As the day went by, I still haven't got the chance. When it was after school, I looked around for Blair, until I spotted her with Serena.

"Hey sis,"I greeted her cause, I knew it bugged her.

"Back off Chuck." Serena splatted back.

"Well someone doesn't want to play today."

Blair looked at Serena then to me, then back back to Serena with a confused look. After that she spoke up.

"Wait, Chuck is your brother?" she asked

**"**Step Brother." Serena answered as she looked up at the sky.

"Oh, that sucks." Blair said as if I wasn't there.

"Oh, I bet you would love to be my sister to share a showers with me. If you wanted to share showers, all you had to do was just ask."I said with giving her a smirk.

"Eww!" Blair and Serena said together.

"Well I'm going to catch up with Dan.". Well later B." Serena said, "Chuck, promise not to do anything pervie with Blair."

"No promises." I answered back as she walked away.

"Well, it looks like its only me and you, Waldorf. I said

"Yeah, sadly it is." she mumbled.

"Get a drink with me." I demanded her.

"Can't, I have plans." she said.

''What plans are better then getting a drink with me?" I asked raising an eyebrow.

"Well, I'm getting drinks, just not with with you." she answered.

"Oh really?" Then with who?" I asked.

"With Jesse, the guy I met in English class."

"Jessey McCarty?" knowing that already," Your going out with that low-life freak?"

"He happens to be the captan of the football team, and if you would excuse me, I have to go and get ready for my date tonight." Blair said as she got up and walked away.

When she was gone, I got out my phone and called my PA "Hey, Chuck Bass here,. I need you to get information on Jesse McCarty, and where he's going to night."

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**Hey again! Remember to REVIEW!!!!!! I'll try to post up the next chapter as soon as I can. REVIEWS ARE LOVED!!!!!! hope you guys are enjoying your summer. Mine is almost over. :( Until then! Peace out!-xoxocullengurl09**


	4. Chapter 4

**Hey!!!! Sup people! So sorry it's been a while. You see school has started :(. But I'm trying to find time for my fanfics. This chapter took a while to write, also I wrote it a while ago. I think it was like in July, but I didn't have the time to post it up. Anyways thank you guys so much for reading and reviewing!!!!In this chapter it is a little suckish, but I bet some people saw it coming. Well I hope you guys will enjoy this chapter!!! And by the way I'm starting a playlist thing. A playlist is pretty much a playlist of song I listen to while I'm writing the chapter, cause I can't write without music!!! **

**Don't let go- David Archuleta**

**Already gone- Kelly Clarkson**

**Always be my baby- David cook**

**Sad song-Blake Lewis**

**Good Girls Go Bad- Cobra Starship ft. Leighton Meester **

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**B's POV**

When I got home, I went straight up to my room to get ready for my date with Jesse. Not that I want to impress him or anything. Then I walked into  
closet and came out with a shirring party top, with a circle skirt, and with black Christian Louboutin pumps. And with a last touch to make the outfit compete  
a Night lily headband.**(If you want to see the whole outfit go in my profile)**. Then I looked at the mirror, putting on my juicy Couture perfume also  
grabbing my like black clutch. When I walked outside to call a cab, I notice how cold it was, but I didn't bother bringing a jacket. _Smart move Blair,_I thought  
to myself, while rubbing my hands on my arms. Finally moments later a cab came. As I got i I told the cab driver to address Jesse texted me. 30 minutes  
later stopped, and then so, I payed the cab driver. As I closed to cab door, the cab drove off. I looked around. I new I was in Soho. Then I looked at the  
building in front of me. It was a really old bar. _Ugh who would take someone out on a date to this rat hole? _I thought in disgust

As I walked in the rat hole, someone called out ,"Blair!"

I turned where the voice was trailed from. It was Jesse with two other guys. _That's weird. Why would he bring two other guys to this date? _I thought to  
myself as I walked up to them.

"Hey"I greeted them.

"Blair, this is my friends, Chase and David. I just ran into them is it okay if they can hang?" Jesse asked me

"Oh, sure," I said, not wanting to be rude.

"Can I get you anything miss?" The bartender asked.

"I'll have a martini." I told the bartender, as I looked over Jesse, who was having a beer.

After finishing my martini, Chase bought everyone shots, and then another one, and another one. After 3 shot, I was getting dizzy **(well I don't know how strong shots are)**.

"Who's up for another around?" Chase shouted.

"Yeah!" Everyone in the bar shouted back.

"Oh, I think I'm going to past on this on." I said, kinda getting worried that I might end up doing something I will regret doing.

"Whats wrong?" Jesse asked

"I'm not really feeling well," I lied, wanting to go home badly.

"Just have one more shot,and then I'll take you home. I promise." Jesse told as he was handing me the shot.

"Fine." I said grabbing the shot from his hand. After that shot, I got so out of control, I ended up having 15 more shots. I was so dizzy I couldn't even talk or walk straight.

"JJJJJJeessseeeeeeee!!!" I shouted

"Yeah?" Jesse asked, with his breath warming my cheek.

"Whoa," I mumbled as I stumbled over on Jesse.

"Oh," Jesse quickly got to me before I hit the floor."Hey Blair, why won't me and the guys take you to the back room?"

"Um why with Chase and David?" I asked, confused.

"Uh, well they can watch the door, so you won't get disturb." Jesse replied

"Well, I want to stay out-" before I finished the sentence , I was already in the back room. Jesse, Chase, and David were in the room too. The Chase locked the door. At this moment, I knew what was happening._ They're going to rape me_.

"No!!!!!"

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**REMEMBER TO REVIEW!!!!!!!!!!!!!!!! If your not, Ed Westwick will come and kill you. Anyways Reviews are loved!!!!**


	5. AN:I'm so so so sorry!

**OMG!!!!! I'm so so so so so sorry!!! It's been too long, but I'm a little stuck. So I'm going to start writing this chapter druning History class, well cause History is the only class I don't sit in the front of the class. And I'll post it up on Friday. Again I'm so so so so so sorry. I bet you guys hate cause I left off on a cliff hanger. I hope I still have you guys. And I bet you guys hate a/n notes. I just been so busy with school, drama, guys who cheat, homework, end of term, other stories, and family stuff. So again, I'm going to update this Friday.I promise. So do I still have my readers?**


	6. Chapter 5

**A/N: Hey you guys!!!!!! As I promised you guys a chapter by Friday!!! And it's Friday!!!! YAY!!!. And I'm sorry that I didn't review reply you guys' reviews. I was getting really busy. Anyways I wrote this chapter in History. We had a sub that day. He goes on and on and on and on. And won't shut up. And he was really weird cause he thought my sunglasses were my my reading glasses. (I don't even have reading glasses) Well, it's a long story. So, What do you guys think of season 3? I kinda think it's a little boring. I'm sorry, but it's just Zzz....... But I'm still watching. I don't know why. Anyways I bet you guys are dieing to know whats going to happen next so here it is!!! And I want to give a big thanks to everybody to review!!!!**

**warning: this chapter has raping **

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**C POV**

As I walked back and forth, waiting for Mike to call. Then my phone rang.

"Bass" I answered.

"Mr. Bass?" I got it." My P.I, Mike said. "Jesse James McCarty. 18, goes to the same school as you. People say that he is dangerous. Also have gotten 3 girls pregnant.

"So where is he tonight?" I asked incipiently. Rushing before he gets his hands on Blair.

"He's at a bar called Izzy, in Soho. **(Can't think of a name so I looked for the closest thing to me which was the Izzy I was drinking)**" Mike said.

"Well That's all I need. Goodbye Mike." I told the man. Then hung up.  
After hanging up, I went straight out of my room, and outside to my limo.

"Get me to a bar, Izzy in Soho." I told my Driver.

_What if this Jesse dude makes a move on Blair? What if he get his hands on her? Or even worse?_ I thought, shaking out thought out of my mind.

"Oh, and step on it." I gave my driver the command.

Minutes later the limo door opened. "We're here Mr. Bass." The driver said.  
I got out of the car, And walked into the was pretty small. Kinda packed. As I looked around around the room, I sadly didn't see the pettie brunette in site.

"Hey, have you seen a little brunette, like this high?" I asked the bartender.

"Yeah, she's in the back room with 3 other guys." The bartender answered  
Then, I panicked. _Oh, god. 3 guys? Shit. _I thought to myself.

"Oh, okay, Thanks" I said to the bartender. Then ran off to find the back room.

**B POV**

At this point, I wanted to die. I always had a bad feeling about Jesse. All three guys got closer. I was panicking, thinking what to do to save myself.

"Help!" I yelled.

"Shut up, bitch." Jesse said, slapping me across my face, hard. Making me gasp in pain and flew to the ground.

"Get up!" One of the guys said, I couldn't tell who cause everything was getting to blurry. They must have put something in my drink.

"I said get up!"The voice said again.  
when I tried to get up, there was a shock of pain, bolting down my body and couldn't move. I was laying there on the ground wait to die. But this was only the beginning. One of the guys grabbed me by the arm and pulled me up roughly like i was a ragged doll.

"Hhhelp" I tried to yell, but it came out with a little whisper.

"Shut up!" One of the guys said, and punched me in the face. Then I blacked out.

**C POV**

I wonder round the hall way trying to find the back room. All on the suddenly heard voices.  
"You get her neck, you get her chest, and i get her ass."  
"Are you sure she's out cold?"  
"Yeah."  
"okay, lets go."

When I heard the end of the conversation i rushed to the door as fast as i could. The door was locked.  
"Fuck" I mumbled under my breath. _Great what should I do now? _I looked around for a solution.  
_Ram it_.

I was now baking out to ram it. Then I let out a sigh. _This is going to hurt like a bitch _I thought as I ran towards the door. Moments later the door busted open. I in the room, saw Blair covered by 3 guys. One guy was licking her neck, the other one had his hands up under her shirt, and the last on had his hands on her legs, making his way up under her skirt.  
At the point I was mad. I rushed over to the guys and the brunette being raped, grabbed one of the guys and punched him in the face. After that I pulled the other guy of of Blair and kicked him in the balls. And lastly the other one in the stomach.

"What the hell?" One of the guys yelled while wiping the blood of his face. The two other guys got up and laid their eyes on me.

"Chuck Bass?" One of the guys that I think is Jesse question."Wow, I'm shocked. I mean the biggest womenizer I know is trying to save a girl being raped."

"Shut up" I spat

"I bet you were going to rape her yourself"

"I said shut up!" I shouted pushing Jesse towards the wall. Jesse slammed against the wall with a loud boom. As Jesse got weakly he said "Chase, David, get him."

"Fuck" I cruised, as the two guys ran toward me. I grabbed the nearest thing to me to defend myself .It was a beer bottle. I grabbed it and smashed it against a table. And pointed the sharp ends of the bottle towards them. Then the two guys froze .

"Dude your crazy." One of the guys said "Let's get get out of here, Chase."  
They both ran out of the room, leaving Jesse behind. Jesse got up and quickly ran over Blair, and was about to pick her up.

"Don't you dare touch her." I snapped.

"What are you? Her girlfriend?"Jesse snapped back.

"Uh..." I awkwardly paused.

"What ever. I'm out."" Jesse said walking out of the room.

The next happen was my eyes were on Blair. She was still lying there and haven't move since the scene that recently happen. I walked over to her and bent down.

"Blair." I whispered in her hair. There was no respond.

"Blair" I whispered again, this time shaking her lightly. Then I realized that she was still out cold.

I let out a loud sigh._ Great now what should I do. I can't just leave her. Great I'm so going to regret this._ I let out another sigh. I slid my hands under Blair's little body, felt a little shock, lifting her up bride style. Then walked out of the room, and out of the bar, straight to the limo. I was still holding her as I got in the limo. I lied her to me. with her head on my lap, surprisingly not thinking this sexual. A piece of hair fell on her face. I reached down to her face and pushed the piece of hair behind her ear. As I was doing that, I felt a sparks when I touched her face.

_What the hell was that?_ I thought. But then I ignored it. Then I felt something fluttering in my stomach. I tried to ignore that too, but it was too strong to ignore. As the limo went on, I stared at Blair the whole ride. A couple minutes later the limo stopped and the door opened.

"Mr. Bass" The driver said opening the door.

I got out of the limo with Blair still in my arms. Walking inside of the Palace towards my suite. When I got in my suite, I walked in my bedroom and laid Blair on my bed and tucked her in.

"Goodnight, Blair " I whispered in her ear, and kiss her on the cheek.

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**A/N: YAY! There it is!!! Yeah, I know, sucky chapter. *sigh* Trying to get better. And I know you guys didn't have rapping in mind but I want Chuck and Blair to be really close. Anyways have any of you guys seen the Stepfather? I did! I saw it last week. And it was AWESOME!!!!! Best scary movie ever!!!!! I screamed like 5 times while my older sister screamed like 100. You guys have to see it! And Pen was hella hot in it!!! Anyways Happy early Halloween!! What are you guys going to be? I'm going to be Rosalie Hale Cullen from Twilight. Well I'll update very soon if you guys review!!! So REVIEW!!!!!!!!! Or jenny will birch slap you over and over and over!!!! JK LOL. But, really please review! It will make my day!! And have a safe happy halloween!!**


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